Isopropanol → HCID 63895443, compound

Temperature

-78 °C

A stirred mixture of 1-bromo-3-methoxy-benzene (1.49 g, 8.0 mmol) and dry THF (20 mL) was cooled to −78° C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (3.0 mL, 7.6 mmol) and stirred for 20 min. Then a mixture of benzo[1,3]dioxole-5-carbaldehyde (1.03 g, 6.8 mmol) in dry THF (15 mL) was added and stirred for 1 hour at −78° C. The mixture was quenched with isopropanol (3.5 mL, 46 mmol) and added water (10 mL). The mixture was extracted with EtOAc (3×40 mL). The combined organic phases were washed with water (2×40 mL), dried over MgSO4 and concentrated to give benzo[1,3]dioxol-5-yl-(3-methoxy-phenyl)-methanol as an oil (2.23 g, 113% crude yield). The product was used in the next step without further purification.

1. customevacuated
2. additionrefilled with nitrogen for 10 cycles
3. additionwas added
4. stirringstirred for 1 hour at −78° C
5. extractionThe mixture was extracted with EtOAc (3×40 mL)
6. washThe combined organic phases were washed with water (2×40 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated

ORD record

ord-fee3c555fc33482fa5c379514d569065

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470723B2